CN103449986A - Method for preparing high-purity 2,4'-difluorobenzophenone - Google Patents
Method for preparing high-purity 2,4'-difluorobenzophenone Download PDFInfo
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- CN103449986A CN103449986A CN2013104477015A CN201310447701A CN103449986A CN 103449986 A CN103449986 A CN 103449986A CN 2013104477015 A CN2013104477015 A CN 2013104477015A CN 201310447701 A CN201310447701 A CN 201310447701A CN 103449986 A CN103449986 A CN 103449986A
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- fluorobenzene
- purity
- high purity
- difluoro benzophenone
- recrystallization
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- 238000000034 method Methods 0.000 title claims abstract description 29
- LKFIWRPOVFNPKR-UHFFFAOYSA-N (2-fluorophenyl)-(4-fluorophenyl)methanone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=CC=C1F LKFIWRPOVFNPKR-UHFFFAOYSA-N 0.000 title abstract description 13
- 239000002904 solvent Substances 0.000 claims abstract description 24
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims abstract description 19
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims abstract description 19
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- RAAGZOYMEQDCTD-UHFFFAOYSA-N 2-fluorobenzoyl chloride Chemical compound FC1=CC=CC=C1C(Cl)=O RAAGZOYMEQDCTD-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000002994 raw material Substances 0.000 claims abstract description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 230000007062 hydrolysis Effects 0.000 claims abstract description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 238000001953 recrystallisation Methods 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 238000004821 distillation Methods 0.000 claims description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 7
- 238000002425 crystallisation Methods 0.000 claims description 7
- 230000008025 crystallization Effects 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract description 9
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 150000001875 compounds Chemical class 0.000 abstract description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 abstract 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
- JWUCHKBSVLQQCO-UHFFFAOYSA-N 1-(2-fluorophenyl)-1-(4-fluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanol Chemical compound C=1C=C(F)C=CC=1C(C=1C(=CC=CC=1)F)(O)CN1C=NC=N1 JWUCHKBSVLQQCO-UHFFFAOYSA-N 0.000 description 5
- 239000005787 Flutriafol Substances 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 239000012535 impurity Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000007818 Grignard reagent Substances 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 150000004795 grignard reagents Chemical class 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminium flouride Chemical compound F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 1
- 241000221785 Erysiphales Species 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- 229930182558 Sterol Natural products 0.000 description 1
- -1 acyl cation Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- GNDHXHLGYBJDRD-UHFFFAOYSA-N bis(2-fluorophenyl)methanone Chemical compound FC1=CC=CC=C1C(=O)C1=CC=CC=C1F GNDHXHLGYBJDRD-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 230000017858 demethylation Effects 0.000 description 1
- 238000010520 demethylation reaction Methods 0.000 description 1
- VQCKMJZSZCVKQT-UHFFFAOYSA-N dichloromethane fluorobenzene Chemical compound ClCCl.FC=1C=CC=CC1 VQCKMJZSZCVKQT-UHFFFAOYSA-N 0.000 description 1
- 238000007336 electrophilic substitution reaction Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000002328 sterol group Chemical group 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for preparing high-purity 2,4'-difluorobenzophenone. The method for preparing the high-purity 2,4'-difluorobenzophenone is characterized in that one or more kinds of compound solvent such as fluorobenzene, dichloromethane, dichloroethane, normal hexane and nitrobenzene are used during a synthesis process, fluorobenzoyl chloride and the fluorobenzene are used as raw materials, and aluminium trichloride is used as the catalyst; after the reaction is finished, hydrolysis and desolventizing are conducted, aftertreatment and recrystallizatoin are conducted and then a high-purity target object is obtained, wherein the mass part ratio of raw materials which are the fluorobenzoyl chloride and the fluorobenzene and the aluminium trichloride is 1:1 to 3:0.5-1.5. The method for preparing the high-purity 2,4'-difluorobenzophenone is simple in synthetic route, environmentally friendly, low in cost, high in productive rate, and suitable for industrialized production.
Description
Technical field
The invention belongs to cleaner production, technical field of chemistry and chemical engineering, relate to the synthetic of high purity flutriafol intermediate, more specifically say a kind of 2, the preparation method of 4'-difluoro benzophenone.
Background technology
Flutriafol by the exploitation of Britain prompt sharp Kanggong department is sterol demethylation inhibitor, is the wide-spectrum bactericide of plant leaf and fringe, effective to cereal Powdery Mildew, Gerlachia oryaae, leaf spot and rust.At present, the method for synthetic flutriafol mainly contains two kinds: a kind of is the grignard reaction method, and this method grignard reagent is difficult for preparation, and yield is low, and the reacting because steric hindrance reason productive rate is also lower of grignard reagent and ketone, and the method is eliminated gradually; Another kind is the carbonyl reduction method, and by synthetic 2,4'-difluoro benzophenone, the steps such as reduction prepare flutriafol, and the method preparation method is simple, and yield is high.Therefore, find a kind of environmental protection, easy and simple to handle and to make the synthetic route of high purity target product necessary.
Mainly by friedel-crafts acylation reaction, prepare 2 both at home and abroad at present; the 4'-difluoro benzophenone; reaction is classical; seem simple; actually operating gets up to have certain difficulty; because the mechanism of friedel-crafts acylation reaction is undertaken by E2 mechanism; form the acyl cation intermediate; therefore, the ortho position substitution product 2 of fluorobenzene, the 2'-difluoro benzophenone inevitably generates; be unfavorable for the purification of product; single magazine content is difficult to be controlled, single assorted content >=1.1%(reference: Meng Lingfeng. synthetic [D] of flutriafol. and Hangzhou: Zhejiang University, 2006.).
Summary of the invention
The technical problem to be solved in the present invention will overcome that 2,4'-difluoro benzophenone production cost is higher, purity is low exactly, the unmanageable problem of single foreign matter content.Use the present invention to prepare 2, the 4'-difluoro benzophenone, low cost of manufacture, product purity high (>=99%), single impurity few (being mainly 2,2'-difluoro benzophenone, content≤0.5%), environmentally friendly.
The present invention, for solving the problems of the technologies described above, provides following technical scheme,
A kind of 2, the preparation method of 4'-difluoro benzophenone, is characterized in that, use one or more complex solvents when synthetic, take o-fluoro-benzoyl chloride and fluorobenzene as raw material, aluminum trichloride (anhydrous) is made catalyzer, after reaction finishes, the hydrolysis precipitation obtains the high purity target product after aftertreatment, recrystallization; O-fluoro-benzoyl chloride wherein: fluorobenzene is raw material: the ratio of weight and number of aluminum trichloride (anhydrous) is 1 ﹕ 1-3 ﹕ 0.5-1.5.
Last handling process of the present invention is: after 1) adopting distillation to remove organic solvent, cooling crystallization makes high purity; 2) after adopting distillation to remove organic solvent, make high purity 2 by the method for recrystallization, the 4'-difluoro benzophenone.
Recrystallization solvent for use of the present invention is: the mixture of methyl alcohol, ethanol, ethylene glycol, Virahol and water, sherwood oil, methyl tertiary butyl ether, tetrahydrofuran (THF) or normal hexane.
The volume ratio of the mixture of methyl alcohol of the present invention, ethanol, ethylene glycol, Virahol and water is 1:1-4,1:1-4,1:1-4,1:1-4.
Synthetic route of the present invention is as follows:
It is starting raw material that o-fluoro-benzoyl chloride and fluorobenzene are take in the present invention, uses solvent described in synthetic route, under the catalysis of anhydrous aluminum trifluoride, carries out Fu-Ke acylations electrophilic substitution reaction and prepares high purity 2, the 4'-difluoro benzophenone.
Innovative point of the present invention is:
the waste water produced in technique after treatment, makes the aluminum chloride complex compound, and can be used for water purification turns waste into wealth, environmental friendliness;
Embodiment
The following examples can make the present invention of those skilled in the art comprehend, but do not limit the present invention in any way, and the present invention's fluorobenzene used, aluminum chloride, o-fluoro-benzoyl chloride all have commercially available.
Embodiment 1
Synthetic (fluorobenzene is made solvent) of 2,4'-difluoro benzophenone
360.0g fluorobenzene and 120.0g aluminum chloride are added in the 500ml reaction flask, under ice bath, hierarchy of control temperature is 10 ℃ of left and right, drip the 118.9g o-fluoro-benzoyl chloride, in the dropping process, system temperature is controlled at 25 ℃, drip and finish, room temperature reaction, gas phase tracks to reaction and finishes, then reaction solution is added in 260ml frozen water and 90ml concentrated hydrochloric acid, separate organic phase, organic phase is used the 100ml water washing again, separate organic layer, then extremely neutral with 100ml 10% sodium hydroxide solution and 200ml washing organic layer respectively, fluorobenzene is reclaimed in air distillation, rectifying obtains product, productive rate 92.5%, content 98.5.Single foreign matter content≤1.1%.
Embodiment 2
Synthetic (normal hexane is made solvent) of 2,4'-difluoro benzophenone
In the normal hexane solvent, take o-fluoro-benzoyl chloride and fluorobenzene as raw material, aluminum trichloride (anhydrous) is reacted as catalyzer, and reaction is poured reaction solution into 2molL after finishing
-1hydrochloric acid soln in, adjust pH to 3, then, with 5% sodium hydroxide solution tune pH to 12, separate organic phase, water with solvent extraction for several times, merges organic phase, after adopting distillation to remove organic solvent, rectifying makes 2,4'-difluoro benzophenone or cooling crystallization makes 2,4'-difluoro benzophenone; Wherein mole proportioning of o-fluoro-benzoyl chloride, fluorobenzene and aluminum trichloride (anhydrous) is 1:1:3.The few content 0.45% of single impurity.
Embodiment 3
In the ethylene dichloride solvent, take o-fluoro-benzoyl chloride and fluorobenzene as raw material, aluminum trichloride (anhydrous) is reacted as catalyzer, and reaction is poured reaction solution into 4molL after finishing
-1hydrochloric acid soln in, adjust pH to 2, then with 8% sodium hydroxide solution, adjust pH to 13, separate organic phase, for several times, the merging organic phase, obtain product 2 through aftertreatment, the 4'-difluoro benzophenone in solvent extraction for water; The recrystallization solvent for use is sherwood oil.Wherein mole proportioning of o-fluoro-benzoyl chloride, fluorobenzene and aluminum trichloride (anhydrous) is 1:3:1, the few content 0.46% of single impurity.
Embodiment 4
Synthetic (methylene dichloride, ethylene dichloride or normal hexane are made solvent) of 2,4'-difluoro benzophenone
Under different solvents, the raw material charging capacity is as following table:
| Title | Quality/g |
| O-fluoro-benzoyl chloride | 118.9 |
| Aluminum trichloride (anhydrous) | 120.0 |
| Fluorobenzene | 79.3 |
| Methylene dichloride | 300 |
| Ethylene dichloride | 300 |
| Normal hexane | 200 |
One of three kinds of solvents of respective quality in 79.3g fluorobenzene, 120.0g aluminum chloride and table are added in the 1000ml reaction flask, under ice bath, hierarchy of control temperature is 10 ℃ of left and right, drip the 118.9g o-fluoro-benzoyl chloride, in the dropping process, system temperature is controlled at 15-25 ℃ of left and right, drip and finish, room temperature reaction, gas phase tracks to reaction and finishes, then reaction solution is added in 260ml frozen water and 90ml concentrated hydrochloric acid, separate organic phase, organic phase is used the 100ml water washing again, separates organic layer, then respectively with 100ml10% sodium hydroxide solution and 200ml washing organic layer
To neutral, solvent is reclaimed in air distillation, and underpressure distillation obtains product.Experimental result is as following table:
| Solvent | Reclaim solvent quality/g | Quality/g | Productive rate/% |
| Methylene dichloride | 249.5 | 149.6 | 91.4 |
| Ethylene dichloride | 278.9 | 151.2 | 92.1 |
| Normal hexane | 170.2 | 151.1 | 92.0 |
Through different solvents, make 2, the 4'-difluoro benzophenone, through GC testing product content all more than 98.0%, single foreign matter content≤1.1%.
Product purity and single foreign matter content result are as following table:
| Solvent | Purity/% | Single impurity/% |
| Methylene dichloride | 98.2 | 1.0 |
| Ethylene dichloride | 98.4 | 1.1 |
| Normal hexane | 98.3 | 0.8 |
| Fluorobenzene | 98.5 | 1.1 |
Embodiment 5
Experimentation is as embodiment 1 or 2, and after vacuum distillation recovered solvent, post-treating method is respectively through cooling crystallization or different solvents recrystallization, gained 2, and 4'-difluoro benzophenone purity and single assorted content are as follows:
Remarks: cooling crystallization or different solvents recrystallization products therefrom analytical procedure are the HPLC method.
Embodiment 6
This technique and tradition 2,4'-difluoro benzophenone preparation technology's similarities and differences:
Identical point: synthetic method is basic identical, is all to adopt friedel-crafts acylation synthetic;
Difference: the last handling process difference, utilize this character of 2,4'-difluoro benzophenone fusing point, adopt the Methods For Purification target product of cooling crystallization or recrystallization, and single magazine is few initiatively, purity is high, and operational path is more suitable for suitability for industrialized production.
This technique is as follows with the product purity contrast table that other companies make:
| Technique or Business Name | Purity |
| This technique | ≥99.0% |
| Lark prestige Science and Technology Ltd. | ≥97% |
| Shanghai Mai Ruier chemical technology company limited | ≥95% |
Claims (4)
1. one kind prepares high purity 2, the method of 4'-difluoro benzophenone, it is characterized in that, use one or more complex solvents when synthetic, take o-fluoro-benzoyl chloride and fluorobenzene as raw material, and aluminum trichloride (anhydrous) is made catalyzer, after reaction finishes, the hydrolysis precipitation obtains the high purity target product after aftertreatment, recrystallization; O-fluoro-benzoyl chloride wherein: fluorobenzene is raw material: the ratio of weight and number of aluminum trichloride (anhydrous) is 1 ﹕ 1-3 ﹕ 0.5-1.5.
2. preparation method claimed in claim 1, described last handling process is: after 1) adopting distillation to remove organic solvent, cooling crystallization makes high purity 2, the 4'-difluoro benzophenone; 2) after adopting distillation to remove organic solvent, make high purity 2 by the method for recrystallization, the 4'-difluoro benzophenone.
3. preparation method claimed in claim 2, wherein the recrystallization solvent for use is: the mixture of methyl alcohol, ethanol, ethylene glycol, Virahol and water, sherwood oil, methyl tertiary butyl ether, tetrahydrofuran (THF) or normal hexane.
4. preparation method claimed in claim 2, the volume ratio of the mixture of wherein said methyl alcohol, ethanol, ethylene glycol, Virahol and water is 1:1-4.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111440058A (en) * | 2020-03-29 | 2020-07-24 | 吉林省中研高分子材料股份有限公司 | Preparation method of high-purity 4, 4' -difluorobenzophenone |
| CN113831231A (en) * | 2021-09-24 | 2021-12-24 | 天津科技大学 | Method for preparing ultra-pure 2,4' -difluorobenzophenone by melt crystallization |
| CN113956141A (en) * | 2021-11-09 | 2022-01-21 | 济源市恒顺新材料有限公司 | Method for producing difluorobenzophenone |
| CN114805040A (en) * | 2022-04-20 | 2022-07-29 | 江西永通科技股份有限公司 | Preparation method of 2, 4' -difluorobenzophenone |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040171895A1 (en) * | 2001-03-12 | 2004-09-02 | Earle Martyn J. | Process catalysed by bis-triflimide compounds |
| CN101429177A (en) * | 2008-12-09 | 2009-05-13 | 江苏七洲绿色化工股份有限公司 | Process for producing bactericide of flutriafol midbody |
-
2013
- 2013-09-27 CN CN201310447701.5A patent/CN103449986B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040171895A1 (en) * | 2001-03-12 | 2004-09-02 | Earle Martyn J. | Process catalysed by bis-triflimide compounds |
| CN101429177A (en) * | 2008-12-09 | 2009-05-13 | 江苏七洲绿色化工股份有限公司 | Process for producing bactericide of flutriafol midbody |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111440058A (en) * | 2020-03-29 | 2020-07-24 | 吉林省中研高分子材料股份有限公司 | Preparation method of high-purity 4, 4' -difluorobenzophenone |
| CN113831231A (en) * | 2021-09-24 | 2021-12-24 | 天津科技大学 | Method for preparing ultra-pure 2,4' -difluorobenzophenone by melt crystallization |
| CN113956141A (en) * | 2021-11-09 | 2022-01-21 | 济源市恒顺新材料有限公司 | Method for producing difluorobenzophenone |
| CN114805040A (en) * | 2022-04-20 | 2022-07-29 | 江西永通科技股份有限公司 | Preparation method of 2, 4' -difluorobenzophenone |
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